Moonlighting Pt. 01

"Hey!" Vinnie called back. Nick turned around.

"What's up?"

"Do you expect her back soon?"

"Maybe..." Vinnie couldn't get a read on this guy but knew Sierra liked him so he tried to behave himself under his own frustrations.

"Can you tell her I stopped by, I just wanted to talk to her about something is all."

"Yeah, sure..."

"Cool."

And with that Nick was gone, Vinnie left only with a new sense of curiosity surrounding the mysterious boy next door.

--

Sierra was currently sitting in her underwear on a chair while she watched one of the other girls, Nikki, getting fucked.

The guy, one of Nikki's regulars, fucked her mercilessly from behind while furiously attacking her clit. It was hard for Sierra not to give in to her carnal desires, but recently she had found that she was comfortable slipping her hands into her pants while watching the fun unfold in front of her. She had told the clients that she was merely a bystander and would not participate with anyone other than herself. This was fine with mostly everyone. But this guy, Jack Pitts, a famous skateboarder in the area, had grown fond of Sierra.

This was fine, Sierra thought, because Jack had a big dick and had never made a move on her. She liked that he watched her touch herself through her clothes while he fucked her friend like a dog.

"So... you want to have any fun tonight little girl?" he asked.

"You already know the answer," she replied, never missing a beat while she rubbed her pussy beneath her shorts and underwear.

"Besides, I like watching you fuck Nikki," she added. She looked at Nikki who was lost in throws of passion, bridging on orgasm.

"Fine, but will you at least come here for a second?"

Sierra just looked warily at him. She was walking a fine line now.

"I won't bite," he added. Sierra considered and than got up. He approached him he held out his hand, which she eventually took.

He pulled her slightly closer to him and looked down into her eyes. He wasn't sure what his game was until he grabbed her hand and held it up to his face - the same hand she had just had down her pants and inside her pussy. He smelled her fingers and she was immediately taken aback by the fact that he now knew exactly what she smelled like. It actually turned her on as much as it shocked her.

"Wow..." was all he could say.

He pulled out of Nikki and she instinctively jumped to her knees in front of his cock while he began jerking off in front of her face.

"Watch this," Jack managed as his dick exploded and cum shot out all over Nikki's freckled little face and splattered onto her forehead, her cheeks, the bridge of her nose, and across her eyes and lips. Sierra had seen guys do this before and didn't get it at all, but Nikki was in the zone pretending to love every second of it, as if the physical act turned her on somehow.

She wondered how many times he masturbated that night thinking of the scent of her soaking wet pussy...

--

Nick was cleaning the dishes when someone knocked on his door. He went to answer it.

It was Sierra.

"Hey!" he said, half nervous and-half excited.

"Hey, so -- I hear you were looking for me," she said.

"Yes. Come in," he said, gesturing for her to enter his small apartment that he finally had cleaned. He took her coat and was stung by the fact that she was only wearing a bra as a top now.

"Can I get you anything to drink?"

"Oh, I'm good." She admitted.

"Cool."

"So..." Sierra said.

"So..." Nick repeated.

"What's up?" She almost began laughing through the awkward silence.

"Well, I was wondering if I could cash in that rain check you promised, but under a different circumstance."

"Oh?" her curiosity was immediately peaked.

"Do you do... uh... photos?" Nick nervously began.

"Photos?"

"Like, let people take your photo? Nude?"

Sierra stopped. She had never taken a nude photo of herself or let anyone else do it. Nobody had ever asked. And now that she had been, she realized quickly that the situation she always feared would finally arise had and worst of all... she was not prepared. Did she have the fortitude to stick to her guns? Could she walk away? She did well enough with Nikki earlier in the night. Why not now? What was so different about this guy?

"I..." she began.

"I offended you -- I'm sorry! I shouldn't have said anything!" he blurted out.

"No! No -- it's just, nobody has ever taken my photo... naked," she admitted honestly enough.

"Come on..." He didn't believe her.

"Serious."

"Well... would you be interested?"

She honestly considered and then suddenly got confused. "Why a photo if you can have the real thing?

"Well it's for a school project"

"A school project?" she asked, not really believing him.

He explained it to her.

"Sounds hot. Uh... wow... well..." she realized this would be the perfect opportunity to get some information out of him for her project.

She swore she'd never cross this line, but it wasn't actually sex, and she was egging him on from day one for this reason... so why not go with it? After all, she wasn't from Los Angeles, and was sure nobody would ever recognize her or even put two and two together if they thought they had. He would just explain the girl in the photo was a prostitute named Sierra, not a humble Sociology grad student named Kendra White.

"I'll make you a deal. I'll let you take my picture anyway you want, but you have to answer my questions no matter what I ask -- completely honestly."

Nick shrugged. "Sure."

"Deal?"

"Deal."

They shook hands immediately. She had him right where he wanted him.

Chapter 4: Questions

Sierra had finally asked Nick for that drink and found herself knocking back her second beer before Nick was even done setting up the lights in the bedroom. It was going to take place on his bed of all places, and she needed to get comfortable with that fact very quickly (along with her own nudity in front of a pseudo-stranger too). She stood by and decided to cut the awkward tension by starting the festivities early.

"So. First question. Have you ever had a girlfriend?"

"Sure."

Nick finished and looked up at Sierra.

"Okay, I'm ready. You can, uh, take your clothes off..."

Sierra slipped her socks off one at a time, keeping her eyes locked with his the whole time.

"How long did your most serious relationship last?"

"Two and a half years. Give or take. Her name was Ashley."

She undid her belt and pulled it from the loops.

"Did you two... make love?"

"Yes, about two months in."

Sierra unbuckled her pants and saw that Nick was in a trance, completely stoned on the idea of her naked before him in the near future. She slowly slipped her pants off and stepped out of them.

She was now standing in just a thong and bra now.

"You have a really amazing body, you know?" Nick said, while trying to take in her ass from behind. The thong she wore left little to the imagination and she could tell he wanted a better view. She helped him out by turning around to show him -- she had a tight little bubble butt that Nick couldn't help but reach out and touch ever so gently.

"Hey now..." she smiled. "Sorry..." he replied. She secretly didn't mind.

"Thanks. So, did your girlfriend let you get away with anything kinky?"

"Depends..."

"What was your favorite thing to do sexually with her?" Sierra prodded.

"My, my you're pushy."

"Hey, I'm about to get naked in front of you!" she reminded sternly.

Nick smiled. "I don't know -- I just don't know what's appropriate."

"I'm a prostitute, trust me -- I've heard and seen it all before."

"Uh, well... I liked when she was giving me head and would let me cum in her mouth... okay? I liked watching her swallow me."

With that, Sierra unhooked her bra and let it fall to the floor revealing her perky little breasts with small dark nipples. They were the perfect size on her tiny little body. Nick froze. Sierra had never exposed herself to someone she had not been in a long-term relationship before -- especially under the hot lights like this. It had always been under the covers before...

"What's your favorite thing to do sexually period?"

"Uh... well, I like to go down on girls."

"Oh? Why?" This answer intrigued her.

"I don't know, I just like everything about it. I like knowing what a girl's most private area looks like and knowing what she smells and tastes like. It's just a really big turn knowing something so intimate and off limits." he explained.

"Wow... that was so hot." She breathed.

"Yeah..."

Sierra then hooked her fingers in her panties and slipped her thong off revealing her completely smooth and freshly shaved pussy.

There wasn't a hair on her body down there. She really liked to look the part. She had always kept herself well maintained down there in the past, but when she started really getting into this whole gig, she realized she had better be ready for anything and just shaved it all off. Truth be told, she loved it and it kind of made her feel like a slut when she looked in the mirror.

"Wow... you're shaved." Nick managed.

"Yeah, do you like?"

"I love it!"

"Did your ex shave?"

"Not completely... she had a landing strip." Nick admitted.

"So how do you want me?"

"Uh... over on the bed..."

Sierra strutted over and sat down on the bed, keeping her legs close together. Nick was able to make out her lips and clit ever so carefully. Sierra sat down finally and stared back down at Nick.

"Do you mind if I ask you some questions?" Nick asked.

"No... I suppose not." Sierra retorted.

"What's your favorite thing to do sexually?"

Sierra had to think... she really didn't know. But then it hit her.

"I like to be on top. What's one thing you've always wanted to do with a girl, but haven't gotten a chance to?"

"That's easy... but you might think it's degrading."

"Try me."

"I want to cum on a girl's face."

"What is it with guys and that!" Sierra exclaimed.

"I told you!"

"No, it's just... why do you guys like that anyway?" she asked.

"It's just... hot... knowing a girl will let you degrade her and look at her so violated. You know, just seeing a girl covered in your seed is hot because you know she's yours from that point on, no matter what," he stated matter-of-factly.

"Ha, quite to the point!" she exclaimed. But she took his answer to heart and saw past the part that grossed her out by the act and saw that it was more about trust than anything else.

"Open your legs..." Nick asked.

Sierra slowly opened her legs as Nick took his camera up and began to snap some photos and stopped when he saw her pussy for the first time -- her tight slit glistening wet.

"Somebody's wet..." he teased.

"Hey, this conversation is hot, I can't help it!"

"Okay move your arm up by your head, yeah just like that!"

She now looked as though posing in a Playboy from the 1950's.

"So... ever thought of me while masturbating?" she asked.

"Ha! Jesus!"

"Come on!"

"Yes! Alright!"

"What do we do when you're jacking off?" Sierra pried.

"You don't want to know if the idea of having a guy cum on your face grosses you out..."

He continued to snap candids of her as her pussy continued to overflow with juices. She was embarrassed by how wet she was getting and knowing she was completely exposed to Nick.

"Oh really!

"Yeah, really!"

Sierra finally found her hands close to her naval.

"Can you put your hand just a little lower, yeah, right there," said Nick. Her fingertips danced lightly below her naval, only inches from her smooth mound. She was starting to breath heavier.

"So, you have your way with me then?"

"And then some..."

"Why don't you take off your clothes too," she suggested.

Nick finally lowered the camera.

"I shouldn't..."

"Why not?"

"I, uh, well..." he stammered.

"You're hard as a rock?"

Nick laughed lightly. "I'm already having difficulty remaining in control..."

"Oh yeah? Well, I'm a big girl, and I want to see what you're clearly straining to hide under there..."

Nick hesitated, and then finally Sierra closed her legs. He sighed and then pulled his shirt off. His toned body struck her immediately. He unbuckled his pants and pulled them off -- his rock hard dick was pitching a tent in his boxers that neither of them could ignore. He was a lot bigger than she had imagined too.

"Wow, somebody's happy to see me," Sierra teased. Nick blushed and finally pulled his boxers off -- his rock hard member pointed right at her and pulsed as if having a mind of it's own. It was well over seven inches long and it looked engorged, almost painful for Nick. Precum formed at the tip and slowly leaked down the side of his shaft.

"Damn!" Sierra said.

Nick walked over to Sierra and sat on the bed next to her. He raised the camera and took some close-ups of her as she slowly began to trace her fingers up and down his sides that sent electric chills up his spine. He took the camera in one hand and slowly started to trace his fingers gently down her arms. He finally set the camera down and looked back at Sierra.

She looked at him curiously as he traced his hands up and down her thighs.

"You finally considering my offer..." she said, not really sure how much further she was going to let things go.

"Very much so," he replied, his cock now in his hands. He slowly stroked himself and let his hands slip over Sierra's small breasts -- air escaped her lungs as her most carnal desires flushed her system.

"I'm too horny... I might get a little rough, and I don't want you to get the wrong idea..."

"I can handle myself..."

Nick was finally overwhelmed by lust.

He dove down between her legs and immediately began licking her soaking wet cunt. She screamed out as Nick began to run his tongue up and down her slit, swallowing all of her juices as fast as he could. He began to eat her like it was the last girl he would ever be with and shoved his fingers deep into her hole at the same time. Sierra slammed back against the bed and her body jolted uncontrollably as sensations she had never felt shot up her spine and hit the most pleasing parts of her brain. Nick started to rub and suck on Sierra's tiny little clit which caused her to yelp like an animal a couple of times, and then he was back to eating her just as quickly.

Sierra bucked her hips rhythmically into Nick's face and quickly wrapped her legs around him.

"How do I taste?" she asked. Nick finally removed his fingers, which were covered in Sierra's sticky juices, and held them up to her face. She looked at them curiously and was bit by the pungent odor of her own pussy that immediately turned her on even more. She took the hint and slowly took Nick's fingers into her mouth and sucked her own precum off of his fingers. It tasted bittersweet, but she loved it. He went back to sucking her pussy dry as she arched her back and quickly began to shake, as if in a seizure.

"Nick, I'm cumming! Oh my God!" Sierra cried out as Nick finally got up and shoved his dick into Sierra's soaking cunt and began to pound away at her like a jackhammer -- Sierra's eyes went wide the second he went inside her and she came down hard on his dick like a vise. She cried out and Nick nearly came himself, but he was able to overcome it as he felt Sierra's pussy clamp down hard on him.

She finally screamed out and her body went rigid as a board... and then she went limp as a ragdoll and he slipped out of her.

"Wow..." she exhaled and fell back onto the bed.

Nick looked into her eyes and down at his throbbing member in his hands, overflowing with precum. It was practically painful at this point.

"You're not done yet," he stated.

"Give me a -- " but Nick had pulled her up to him and stood before her on the bed and quickly shoved his entire length down her throat. She immediately gagged as he started to buck his hips against her head and slowly fucked her face. She reached up and placed her soft hands against his abs to push away, but he just grabbed the back of her head and pulled her closer to him -- his dick sliding deeper into the mouth.

"Can you deepthroat?" he asked, lost in his own pleasure. She just mumbled on his cock. He didn't care what the answer was. He started to pick up the pace and felt a familiar sensation build up deep inside his balls. Finally, Sierra held her hands up, knowing she was powerless against his grip. She was going to let him use her like this, and knew it was about to end anyway.

"Sierra!" he cried out as he slipped from her mouth and stroked himself right in front of her face.

She tried to back away instinctively but he caught her by her hair and forced her head back to his cock just as streams of thick white cum shot out of his dick and painted her face one jet at a time. The cum landed across her hair and face, she felt as though it were raining and couldn't believe how much he was pumping onto her. It never stopped.

"Oh!"

A jet landed in her eye and finally Nick plunged his member back into her mouth and shot the last few loads deep into her throat, forcing her to swallow instantly.

He finally released himself from her mouth and from his deadly grip as she collapsed back on the bed next to him. She stared back at him and saw that he was back to normal, but was looking at her in a new way. She was covered in his cum that dripped down the sides of her face, and knew that this had been his fantasy for some time. She decided not to immediately clean herself up, but let Nick take in his wild fantasy. Still, she felt sick, like she might vomit -- how disgusting this was had not even begun to set in for her.

But she was now his whore, and whatever that entailed... she would abide by.

"Is this what you wanted?" she managed.

"Yes..."

"Do I look like a proper little slut?"

"Like a fucking whore..." he added. She smiled. Nick reached out and wiped some of his cum from the side of her face and fed it to her, she reluctantly accepted and swallowed. She then leaned back and fell victim to tunnel vision -- she was completely drained.

Nick looked over at her and Sierra knew that she would not be getting much sleep that night.

Chapter 6: Crossing The Line

"I hope I wasn't too rough..." Nick asked, genuinely concerned.

"No, I'm just glad you got that out of your system," she smiled back at him while wiping some more of his cum off her face and slipping it into her mouth to turn him on again. She wasn't crazy about the idea of literally eating his seed, but she was playing a part and truth be told, it ruined her tonight. She was no longer herself, but a rather a culmination of countless months worth of character creation -- she had assumed this character's identity now to her very core, the way David Webb became Jason Bourne at the drop of a hat when bullets started flying.

Her real name was Kendra White, and she had only been moonlighting as Sierra in the beginning. Though, as time went on, the fantasies slipped from Sierra's life into Kendra's. Then, the attitude had been affected, and a balance of power slowly shifted within her. Kendra had been tainted now, and the two personalities slowly started to blend together. She was beginning to lose her mind the last couple of weeks, not really sure what she wanted from what life anymore.

But for now, she lost herself to Sierra and was enjoying every minute of it, solely because it was not a life she would otherwise seek out. Only, unlike the other girls, she had the opportunity to walk away whenever it got to be too much.

She was back with Nick...

"Yeah..." he breathed.

Nick was slowly stroking himself while staring at Sierra's nude body. She took note of this and found the idea to be completely erotic. Her most private areas flushed and she felt a tickle inside her that she knew would only lead to trouble.